Whine Up the Hill 2026

Whine up the Hill is a short run/walk at Maple Retreat in Park City, Kentucky, near Mammoth Cave National Park. The main event is timed and competitive, but as the title suggests, it is not quite a 5K, and the course challenges runners with a steep climb. The series also includes a Sip n Stroll and a Kid's Run for ages 6 to 12. The route ascends the hill and continues through a vineyard, with wine stops integrated into the adult course. Local wineries provide tasting tables along the way, and participants 21 or older may sample with ID. This is the second annual edition, highlighting the contrast between a strenuous uphill effort and a relaxed vineyard outing afterward.